The villas are worth more than four stars but not quite worth five stars. Overall, we loved Maui and had a great time. The hotel concierge was slightly difficult to communicate with over emails when asking questions in preparation for our trip. We continuously had multiple emails for simple questions. However, they were very nice about everything, offered good suggestions, and were very responsive with texting when we were on-site.
Our villa (112-2) was spacious and clean. We could easily cook meals in the villa. We grilled burgers one night and had breakfast there every morning. It had indoor and outdoor dining areas and lots of plates, glasses, silverware, cutting boards, etc. However, it had no food storage, Tupperware, or plastic wrap, so it was hard to wrap up leftover food or open packages.
The views from the villa were very nice. The villa was about a half mile from the ocean (based on Apple Watch stats), but it sits high on a hill. We did not have a corner unit (as shown in the pictures online, so there was no wrap-around or two-sided view). There is quite a steep hill that you must walk up and down whenever you go to the Ho'olei clubhouse or the Grand Wailea. If there is anyone in your party with mobility issues, this could be a problem.
The Shops at Wailea are within walking distance from the villa. It has a small grocery store, a shopping mall, and a few restaurants. We went there several times for various things.
Ho'olei Villas offers shuttle services to The Shops at Wailea (and, I'm sure, other places). We only used the shuttle to help us bring our luggage down the steep hill at check-out, but they were very nice. We just texted that we needed a pickup, and they were there within a few minutes.
A big concern for us was crossing a four-lane street from the villas to the Grand Wailea. It has a stoplight and a cross sign. However, I saw two cars run the light after our walk sign was on, so I didn't let my 12 or 14-year-olds cross by themselves. People drove fast on the street between the villas and the Grand Wailea.
The Grand Wailea is huge and has many amenities: many pool spaces, a nice spa (I had a great massage!), restaurants, beach access, shops, and more. We went during Spring Break and it was mainly families staying at the resort.
We rented a poolside cabana for a day (we had Cabana #10). It was expensive but private, and we didn't have to fight for pool chairs (see below). The only drawback is that the cabana didn't face the pool, so it was hard to keep track of the kids. They did deliver snacks throughout the day (popcorn, popsicles, cookies, etc.), which were unexpected treats.
While there were tons of kids and families staying at this resort, some restaurants on site were better than others at children's menu items. We didn't feel like Humuhumunukunukuāpuaʻa had a great children's menu and was ridiculously expensive for what you get. On the other hand, the Luau was very nice. Great pacing of the night with good food, mingling, and performances.
We took advantage of many of the activities and amenities in the area. I ran on the beach path several mornings we were there. It is crowded (even early) but has great views.
Our 12-year-old had a SCUBA lesson and ocean dive and loved it. The lesson takes place at the resort pool, and then they dive in the ocean with the instructor afterward.
The signature massage at the spa at the Grand Wailea was amazing.
We also did a day trip to Honolulu to visit Pearl Harbor. We flew in and out of Honolulu, and while it was a long day, all four of us felt it was worth it. We saw the USS Missouri, the USS Arizona, the Memorial, and the Aviation Museum. All were very impressive, especially the USS Missouri.
Because the resort is so big, it was hard to navigate, even after several days of walking around. We often had a hard time tracking our teenagers down because even the pools are very spread out and on multiple levels.
As with everything in Hawaii, the resort is expensive. We felt a little nicked-and-dimed having to pay $150 for two lounge chairs on the beach for the day. Especially when we were already paying a daily resort fee. There also was no beach food or drink service.
In the morning, it was like the Hunger Games to get pool chairs (pools open at 7 a.m., and people start lining up as early as 6:30 a.m.). Once you get a chair, you're packed in like sardines. I didn't feel like the pool chair setup was on par with the price you're paying for the resort/villa.
One thing to note is that Inspirato says they have The Rock for teens. That has been closed since Covid. Now they have The Cave – a teen game room. It's only open Friday, Saturday, and Sunday from 5 p.m.-9 p.m. We went one night, and it was fun for a bit, but all the games needed some updating. The dart boards, the basketball hoop game, and the foosball table were broken. The games were still usable but weren't working properly.
We did not rent a car for this trip and had no issues walking or taking an Uber anywhere we needed to go (just to and from the airport).
For our family, the Grand Wailea was just too big. We really didn't like having to stand in line before 7 a.m. to make sure we could get pool seats, only to be pushed up against our neighbors. There were too many people for us. While the amenities are nice, you can find other luxury hotels that offer similar, if not better, amenities that aren't nearly as busy.
Maui, and Hawaii in general, is beautiful, and we really enjoyed our week here. There were just some cons that made the trip not quite worth the extra costs associated with staying at a really large resort.